Learning for underserved youth is integral to social progress. Yet, too often, young people experience disconnects between their educational experiences and both individual and community needs. Arts can help these youth recover a unity through collective action in the community. Drawing from the experiences of a 4-year interdisciplinary research project, Youth Community Informatics (YCI), we discuss ways of engaging underserved youth through the interplay between art education and digital media. We use the theory of community inquiry, which is informed by pragmatist philosophy, especially that of John Dewey and Jane Addams. We propose a pedagogical perspective on art education that embraces this conception of community inquiry and illustrate it with practical examples from the YCI project. This view of learning supports the connectedness of individuals and community for underserved youth.